6957-17-1

Basic information

• Product Name: 4-phenylhexan-3-one
• Synonyms: 3-hexanone, 4-phenyl-
• CAS NO: 6957-17-1
• Molecular Formula: C₁₂H₁₆O
• Molecular Weight: 176.2548
• Mol File: 6957-17-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 246.6°C at 760 mmHg
• Flash Point: 92.9°C
• Density: 0.946g/cm³
• Vapor Pressure: 0.0268mmHg at 25°C
• Refractive Index: 1.495
• CAS DataBase Reference: 4-phenylhexan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-phenylhexan-3-one(6957-17-1)
• EPA Substance Registry System: 4-phenylhexan-3-one(6957-17-1)

Safety Data

• Hazardous Substances Data: 6957-17-1(Hazardous Substances Data)

Upstream product

• 41979-19-5 2-ethyl-1,2-epoxy-1-phenyl-butane 
• 5682-46-2 2-Ethylbutyrophenon 
• 1007-32-5 benzyl ethyl ketone 
• 75-03-6 ethyl iodide 
• 20805-09-8 2-ethyl-1-phenyl-butane-1,2-diol 
• 7664-93-9 sulfuric acid 
• 925-90-6 ethylmagnesium bromide 
• 97-93-8 triethylaluminum 
• 811-49-4 ethyllithium 
• 90-27-7 2-Phenylbutyric acid 
• 26164-15-8 (+)-(S)-methyl 2-phenylbutanoate 
• 2294-71-5 methyl 2-phenylbutanoate 
• 40473-35-6 (S)-(+)-2-phenylbutyric acid chloride 
• 26939-22-0 2-benzyl-4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazine 

Downstream Products

• 116809-19-9 R(+)-1-phenyl-1-propyl propionate 
• 19019-92-2 1-phenyl-propyl 
• 6006-69-5 4-phenylhexan-3-ol 

Relevant articles and documents

Nucleophilic α-arylation and α-alkylation of ketones by polarity inversion of N-alkoxyenamines: Entry to the umpolung reaction at the α-carbon position of carbonyl compounds

A new aspect of enamine chemistry: The formation of N-alkoxyenamines from ketones has led to an efficient umpolung reaction. The alkylation of N-alkoxyenamines with trialkylaluminum compounds proceeded smoothly and gave α-alkylated ketones (see scheme). This reaction offers a simple transformation of ketones into α-substituted ketones without the need to isolate enamines and intermediary imines.

Enzymatic kinetic resolution of racemic ketones catalyzed by Baeyer-Villiger monooxygenases

A set of racemic cyclic and linear ketones, as well as 2-phenylpropionaldehyde, were tested as substrates in the enzymatic Baeyer-Villiger oxidation catalyzed by two Baeyer-Villiger monooxygenases: phenylacetone monooxygenase (PAMO) and 4-hydroxyacetophenone monooxygenase (HAPMO). Excellent enantioselectivites (E > 200) can be obtained in the kinetic resolution processes depending on the substrate structure and the reaction conditions. The parameters affecting the biocatalytic properties of these enzymes were also studied, in order to establish a deeper understanding of these novel biocatalysts.

Enantiospecific synthesis of 4-(4'-methoxyphenyl)-hexan-3-one as precursor for optically active (pS) or (pR) isomer of (Z) or (E)-3-(2'-((N,N-dimethylamino)methylferrocenyl)-4-(4''-methoxyphenyl)-hex-3-ene

We describe herein an original method for the preparation of enantiomerically pure (Z)- or (E)-3-(2'-((N,N-dimethylamino)methylferrocenyl)-4-(4''-methoxyphenyl)-hex-3-ene possessing a p(S) or p(R) plane of chirality. The key step of the synthesis lies in obtaining enantiomerically pure (R) or (S) 4-(4'-methoxyphenyl)-hexan-3-one whose reaction with the lithiated N,N-dimethylaminomethylferrocene leads to two enantiomerically pure amino-alcohol diastereomers (pS,3S,4R) and (pR,3S,4R), or (pS,3R,4S) and (pR,3R,4S) respectively. Subsequent dehydration yields a mixture of three olefins, namely, two trisubstituted olefins and either the (Z)- or (E)-tetrasubstituted olefin with respect to the starting amino-alcohol diastereomer. Additionally we obtained the enantiomerically pure (R)- and (S)-4-phenyl-hexan-3-one and the corresponding diastereomeric amino-alcohols.